CareerPlan

Windows Systems Engineer

USAFull-time$93k–$133k2026-10-20 → 2026-10-22
Hybrid

Core

Senior Windows Infrastructure Engineer leading the migration of legacy Windows Server workloads (2008) to modern versions (2019/2022) in an IaaS environment.

Role type

Senior hands-on IC Windows Systems Engineer

Builds

Migrated server workloads, IIS applications, and Windows Services

Domain

Enterprise IT Infrastructure / Windows Server Modernization

Required skills

Windows Server administration, IIS administration, SQL Server dependency management, MSMQ/enterprise queuing, Active Directory, networking fundamentals, root-cause analysis, documentation

Preferred skills

PowerShell scripting, CI/CD tools (TeamCity, Octopus Deploy), Azure IaaS, change-controlled environment experience, security awareness in regulated systems

Technologies

Windows Server, IIS, SQL Server, MSMQ, Active Directory, Azure, PowerShell, TeamCity, .NET

Responsibilities

Migrate applications and server workloads from Windows Server 2008 to 2019/2022; Lead IIS website migrations including application pools and bindings; Migrate and validate Windows Services and dependencies; Assess SQL Server application dependencies; Evaluate and migrate message queues; Identify migration risks and remediation paths; Document environments and migration steps; Coordinate with DevOps and application teams; Troubleshoot post-migration issues

Seniority

Senior, hands-on IC